Total synthesis of (+)-indolizidine 195 B and (+)-monomorine

Tetrahedron Letters

Volumn 37, Issue 1, 1996, Pages 111-114

  Solladié, Guy ^a   Chu, Guo Hua ^a,b  

^a CNRS   (France)

^b SHANGHAI INSTITUTE OF MATERIA MEDICA   (China)

Author keywords

[No Author keywords available]

Indexed keywords

INDOLIZIDINE 195B; INDOLIZIDINE ALKALOID; MONOMORINE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030043676     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02086-1     Document Type: Article

References (22)

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6. For recent syntheses see : a) Jefford, C.W. ; Tang, Q. ; Zaslona, A., J. Am. Chem. Soc. 1991, 113, 3513-3518 ;
7. b) Ito, M. ; Kibayashi, C., Tetrahedron 1991, 47, 9329-9350;
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12. g) Artis, D.R. ; Cho, I.S. ; Jaime-Figueroa, S. ; Muchowski, J.M., J. Org. Chem. 1994, 59, 2456-;
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16. Solladié, G. ; Hutt, J. ; Girardin, A., Synthesis 1987, 173.
17. Solladié, G. ; Almario, A.; Tetrahedron Asym. 1995, 6, 559-576 and cited references.
18. 2O, OH), 4.27 (m, 1H, H-2), 7.33, 7.54 (2d, 4H, J=8.2Hz, arom.H).
19. 4 in ether or THF led to a TBS exchange between the secondary to the primary OH.
20. 3) : δ : 13.7, 20.3, 24.8, 29.7,45.7,49.5, 58.8, 66.6, 66.7, 67.9, 71.6, 127.6, 127.7, 128.2, 136.8, 155.6.
21. Blanchette, M.A.; Choy, W.; Davis, J.T.; Essenfeld, A.P.; Masamune, S.; Roush, W.R.; Sakai, T., Tetrahedron Lett. 1984, 25, 2183-86.
22. 3,5 , a similar stereoselectivity was observed during the formation of the bicyclic indolizidine.